Chzchjcn



- benzophenothiazine series.

BENZOPHENO THIAZINE NITRILES Nathan L. Smith, Indian Head, Md.

No Drawing. Application October 30, 1950, Serial No. 193,016

3 Claims. (Cl. 260-243) (Granted under the act of March 3, 1883, as amended April 30, 1928; 370 O. G. 757) This invention relates to new compounds of the Example To a mixture of parts acrylonitrile and 25 The new compounds of the invention are [3-- arts 7-benzoic] henothiazine was added 0.5 ml. (12 benzo[a]phenothiazine-prop1on1tr1le and B- griton B (40% alzlueous solution). The reaction Lggfl g i gg They 5 proceeds at room temperature and was completed g e or by heating on a steam bath for 1 hour. The

CHZCHION product was taken up in glacial acetic acid and R precipitated therefrom as yellow crystals (M. P. N a m 215 C.) by the addition of water.

The invention described herein may be manufactured and used by or for the Government of s c the United States of-America for Governmental R purposes without the payment of any royalties wherein one of the radicals R is the residue of a 15 33 g f g fused benzene ring or benzo group and the other 1 fii f mon r i nun f is hydrogen. The nomenclature here used is that th g 1 o p Op 0 1 e 0 according to Chemical Abstracts wherein the a e genera 0mm and the c fused positions correspond, respectively, 0111011201 to the N-1,2 and N-3,4 fused positions following R the nomenclature according to Beilstein. a

The new compounds are antioxidants for substances such as gasoline and petroleum lubricants. c

The presence of the benzo group enhances the s solubilities of the phenothiazine molecule in liq- 5 R uid hydrocarbons. They are valuable intermediwherein one of the radicals R is hydrogen and the ates for organic synthesis and in particular for the other is the benzo group in one of the fused posiproduction of the carboxylic acid derivative and tions at and c.

amides and amines. 2. As a new compound, B-(IZ-benzoEalpheno- The preparation of the new mononitriles can be thiazine) propionitrile.

carried out by reaction between acrylonitrile and, 3. As a new compound, fi-(T-benzoEclphenorespectively, 12 benzoEalphenothiazine(thio thiazine)propionitri1e.

phenyl-a-naphthylamine) and 7-benzoiclpheno- NATHAN L. SMITH.

thiazine(thiophenyl-fi-naphthylamine) in the presence of a small amount of Triton B (aqueous REFERENCES CITED solution of benzyltrimethylammonium hydro)" The following references are of record in the ide) which acts to catalyze the addition reaction. me f this patent:

The following specific example illustrates the preparation of the new compounds. Parts are in UNITED STATES PATENTS the metric system and are by Weight unless other- Number Name Date wise indicated. 2,217,566 Smith Oct. 8, 1940 

1. A BENZOPHENOTHIAZINE MONO-PROPIONITRILE OF THE GENERAL FORMULA: 